US4681882A - 4-alkoxy-pyrido[2,3-d]pyrimidine derivatives - Google Patents
4-alkoxy-pyrido[2,3-d]pyrimidine derivatives Download PDFInfo
- Publication number
- US4681882A US4681882A US06/787,844 US78784485A US4681882A US 4681882 A US4681882 A US 4681882A US 78784485 A US78784485 A US 78784485A US 4681882 A US4681882 A US 4681882A
- Authority
- US
- United States
- Prior art keywords
- methyl
- pyrido
- compound
- pyrimidine
- dihydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Definitions
- the invention concerns new 4-alkoxy-pyrido[2,3-d]pyrimidine derivatives of the general Formula I ##STR1## wherein R 1 represents an unsubstituted or substituted aromatic or heteroaromatic ring;
- R 2 represents a nitrile group, a carboxyl group or an alkoxycarbonyl residue with up to six carbon atoms;
- R 3 is a straight-chained or branched alkyl group with up to four carbon atoms or an amino group
- R 4 represents a straight-chained or branched alkyl group with up to four carbon atoms; as well as optionally the pharmaceutically acceptable salts thereof.
- Another subject matter of the present invention is the use of 4-alkoxy-pyrido[2,3]pyrimidine derivatives of the general Formula I for the treatment of vascular diseases and pharmaceutical compositions containing the new compounds.
- the compounds of the present invention may be prepared by a process characterized in that 4-oxopyrido[2,3-d]pyrimidine derivatives of the general Formula III. ##STR2## wherein R 1 and R 3 have the above meaning, and R 2 ' represents a nitrile group or an alkoxycarbonyl residue with up to six carbon atoms, is O-alkylated in a generally known manner.
- the compounds of the general Formula III serving as the starting products are prepared by either:
- the dihydropyridine derivative is heated to temperatures between 50° and 160° C., preferably 100°-150° C., together with s-triazine in an inert organic solvent in the presence of strong bases such as, e.g., alkali alcoholates or sodium hydride in an inert organic solvent.
- strong bases such as, e.g., alkali alcoholates or sodium hydride in an inert organic solvent.
- Suitable solvents are mainly polar solvents such as dimethylsulfoxide, dimethylformamide or ethyleneglycol dimethylether.
- the reaction (b) is performed by heating the two components in an acid medium, preferably in boiling glacial acetic acid.
- the 4-alkoxy-pyrido[2,3-d]pyrimidine derivatives of the general Formula I are prepared according to the usual processes as described for the O-alkylation of lactams in the literature (cf. "Adv. Heterocyclic Chem.” 12 (1970), 185-212).
- Suitable alkylation agents are alkyl halides and alkyl sulfonates, dialkyl sulfates and trialkyl oxonium salts.
- the compounds of the general Formula III are used in the form of their metallic salts, preferably their alkali salts or silver salts, which are either prepared separately or in situ by means of suitable bases such as metallic hydrides, carbonates or alkoxides in an aprotic solvent.
- suitable solvents are almost all inert organic solvents such as open-chained, cyclic or aromatic hydrocarbons, e.g., n-pentane, n-hexane, cyclohexane, benzene, or toluene, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, ether, such as, e.g., diethylether and 1,2-dimethoxyethane, as well as dipolar aprotic solvents such as dimethylformamide, hexamethylphosphoric acid triamide and dimethylsulfoxide.
- the temperature may vary between -20° C. and the boiling point of the respective solvent.
- the product mixtures thus obtained may be separated by means of chromatography and/or crystallization.
- the 4-alkoxy-pyrido[2,3-d]pyrimidine derivatives of the general Formula I are obtained preferably by reacting the 4-oxo-pyrido[2,3-d]pyrimidines of the general Formula III with trialkyl oxonium salts, in particular trimethyloxoniumtetrafluoroborate, in an aprotic solvent.
- trialkyl oxonium salts in particular trimethyloxoniumtetrafluoroborate
- the compounds of the general Formula I according to the invention have a chiral center at C-5 they may be present either as racemic mixtures, or in the form of the enantiomers.
- the pharmaceutically acceptable salts are obtained in the usual manner by neutralization of the bases with corresponding inorganic or organic acids.
- acids may be used, e.g., hydrochloric acid, sulfuric acid, phosphoric acid, lactic acid, citric acid, malic acid, salicyclic acid, ascorbic acid, malonic acid, or succinic acid.
- unsubstituted or substituted aromatic or heteroaromatic ring there is meant phenyl or phenyl substituted by up to three of the same or different groups selected from a straight or branched alkyl with up to four carbon atoms, halogen selected from fluorine, chlorine, bromine or iodine, nitro, a straight or branched alkoxy with up to four carbon atoms, difluoromethoxy, trifluoromethoxy, dialkylamino in which alkyl is as defined above, alkylthio in which alkyl is as defined above or trifluoromethyl, or a methylenedioxy group; or a pyridyl, e.g., 2-, 3-, or 4-pyridyl, or thienyl group (2- or 3-) which is unsubstituted or substituted by alkyl as defined above.
- halogen selected from fluorine, chlorine, bromine or iodine, nitro, a straight or branche
- R 1 represents an unsubstituted or substituted phenyl residue substituted, preferably in two or three position, by halogen, nitro, methyl, methoxy, difluoromethoxy, trifluoromethoxy, dimethylamino or diethylamino, methylthio or trifluoromethyl, or a phenyl residue disubstituted, preferably in 2,3 position by methoxy or methylenedioxy, or in 2,3 or 2,6 position by halogen atoms, which may be the same or different;
- R 2 represents a nitrile group, a carboxyl group or an alkoxycarbonyl residue, in particular a methoxy, ethoxy, isopropoxy, isobutoxy, or methoxyethoxy carbonyl residue;
- R 3 represents a methyl or ethyl residue or an amino group
- R 4 represents a methyl, ethyl, n-propyl or isopropyl residue.
- the compounds of the general Formula I possess valuable pharmacological properties. In particular they produce calcium-antagonistic effects such as, e.g., termination of smooth-muscle contraction from potassium depolarization induced by calcium.
- the compounds are mainly indicated for the treatment of cerebral, cardiac, and peripheral vascular diseases such as myocardiac ischemia, cerebral infarction, pulmonary thromboses, as well as in cases of arteriosclerosis and other stenotic disorders.
- the 4-alkoxypyrido[2,3-d]pyrimidine derivatives of the present invention are therefore valuable agents for combating cardiovascular mortality.
- Another subject-matter of the present invention is therefore the use of 4-alkoxypyrido[2,3-d]pyrimidine derivatives of the general Formula I in the treatment of vascular diseases.
- the compounds of the general Formula II according to the invention may be applied in liquid or solid form, orally or parenterally.
- solution for injection mainly water is used containing such additives as stabilizers, solubilizers or buffers as are usual for solutions for injection.
- Such additives are, e.g., tartrate and citrate buffers, ethanol, complex formers (such as ethylenediamine-tetraacetic acid and the nontoxic salts thereof) as well as high molecular weight polymers (such as liquid polyethylene oxide) to regulate viscosity.
- complex formers such as ethylenediamine-tetraacetic acid and the nontoxic salts thereof
- high molecular weight polymers such as liquid polyethylene oxide
- Solid vehicles are, e.g., starch, lactose, mannitol, methyl cellulose, talcum, highly dispersed silicic acid, high molecular weight fatty acids (such as stearic acid), gelatin, agar-agar, calcium phosphate, magnesium stearate, animal and vegetable fats, solid high molecular weight polymers (such as polyethylene glycol); if desired preparations for oral application may in addition contain flavors and/or sweetening agents.
- high molecular weight fatty acids such as stearic acid
- gelatin e.g., agar-agar, calcium phosphate, magnesium stearate, animal and vegetable fats
- solid high molecular weight polymers such as polyethylene glycol
- enterally administered single doses are in the order from about 5 to 250 mg, preferably 10-100 mg. Doses for parenteral application would be in the order from about 1 to 20 mg.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19843438351 DE3438351A1 (de) | 1984-10-19 | 1984-10-19 | 4-alkoxy-pyrido(2,3-d)pyrimidin-derivate, verfahren zu deren herstellung und deren verwendung |
DE3438351 | 1984-10-19 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/055,816 Division US4762837A (en) | 1984-10-19 | 1987-05-29 | 4-alkoxy-pyrido[2,3-d]pyrimidine derivatives for treatment of myocardiac ischemia |
Publications (1)
Publication Number | Publication Date |
---|---|
US4681882A true US4681882A (en) | 1987-07-21 |
Family
ID=6248308
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/787,844 Expired - Fee Related US4681882A (en) | 1984-10-19 | 1985-10-16 | 4-alkoxy-pyrido[2,3-d]pyrimidine derivatives |
US07/055,816 Expired - Fee Related US4762837A (en) | 1984-10-19 | 1987-05-29 | 4-alkoxy-pyrido[2,3-d]pyrimidine derivatives for treatment of myocardiac ischemia |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/055,816 Expired - Fee Related US4762837A (en) | 1984-10-19 | 1987-05-29 | 4-alkoxy-pyrido[2,3-d]pyrimidine derivatives for treatment of myocardiac ischemia |
Country Status (14)
Country | Link |
---|---|
US (2) | US4681882A (de) |
EP (1) | EP0180834B1 (de) |
JP (1) | JPS61100582A (de) |
CN (1) | CN1004274B (de) |
AT (1) | ATE45949T1 (de) |
AU (1) | AU579413B2 (de) |
CA (1) | CA1257261A (de) |
DD (1) | DD239794A5 (de) |
DE (2) | DE3438351A1 (de) |
DK (1) | DK478585A (de) |
ES (1) | ES8605519A1 (de) |
GR (1) | GR852529B (de) |
HU (1) | HU194227B (de) |
ZA (1) | ZA857989B (de) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5059602A (en) * | 1990-08-27 | 1991-10-22 | Hoechst-Roussel Pharmaceuticals Inc. | 4-substituted dihydropyrido(4,3-d)pyrimidines as analgesics and topical antiinflammatory agents for the treatment of skin disorders |
WO2003009815A2 (en) | 2001-07-25 | 2003-02-06 | Biomarin Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
WO2006116718A2 (en) | 2005-04-28 | 2006-11-02 | Proteus Biomedical, Inc. | Pharma-informatics system |
WO2008036682A2 (en) | 2006-09-18 | 2008-03-27 | Raptor Pharmaceutical Inc. | Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates |
US20100035902A1 (en) * | 2006-06-07 | 2010-02-11 | Bayer Healthcare Ag | 5-aryl-substituted dihydropyridopyrimidines and dihydropyridazines and use thereof as mineral corticoid antagonists |
WO2010095940A2 (en) | 2009-02-20 | 2010-08-26 | To-Bbb Holding B.V. | Glutathione-based drug delivery system |
US20100305052A1 (en) * | 2006-06-07 | 2010-12-02 | Bayer Schering Pharma Aktiengesellschaft | Substituted 4-aryl-1,4-dihydro-1,6-naphthyridines and use thereof |
WO2012044761A1 (en) | 2010-09-29 | 2012-04-05 | University Of North Carolina At Wilmington | Ladder-frame polyether conjugates |
EP4218718A2 (de) | 2009-05-06 | 2023-08-02 | Laboratory Skin Care, Inc. | Dermale freisetzungszusammensetzung mit wirkstoff-calciumphosphat-partikelkomplexen und anwendungsverfahren |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3438350A1 (de) * | 1984-10-19 | 1986-04-24 | Gödecke AG, 1000 Berlin | 4-oxo-pyrido (2,3-d) pyrimidin-derivate, verfahren zu deren herstellung und deren verwendung |
DE3501696A1 (de) * | 1985-01-19 | 1986-07-24 | Bayer Ag, 5090 Leverkusen | Pyridopyrimidine, mehrere verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4361700A (en) * | 1980-05-20 | 1982-11-30 | James S. Waldron | Pyridopyrimidinone derivatives |
US4560753A (en) * | 1982-11-05 | 1985-12-24 | Sterling Drug Inc. | 2-Substituted-pyrido[2,3-d]pyrimidin-5(8H)-ones |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE525394A (de) * | ||||
US3673184A (en) * | 1970-09-02 | 1972-06-27 | Dainippon Pharmaceutical Co | Certain 2-substituted-5,8-dihydro-5-oxopyrido{8 2,3-d{9 pyrimidine-6-carboxylic acid derivatives |
US4271164A (en) * | 1979-04-16 | 1981-06-02 | Warner-Lambert Company | 6-Substituted-arylpyrido[2,3-d]pyrimidin-7-amines and derivatives |
US4432981A (en) * | 1982-11-05 | 1984-02-21 | Sterling Drug Inc. | 2-(Pyridinyl or hydroxyphenyl)-8-substituted pyrido[2,3-d]pyrimidin-5(8H)-ones |
DE3438350A1 (de) * | 1984-10-19 | 1986-04-24 | Gödecke AG, 1000 Berlin | 4-oxo-pyrido (2,3-d) pyrimidin-derivate, verfahren zu deren herstellung und deren verwendung |
-
1984
- 1984-10-19 DE DE19843438351 patent/DE3438351A1/de not_active Withdrawn
-
1985
- 1985-10-16 CN CN85107614.9A patent/CN1004274B/zh not_active Expired
- 1985-10-16 US US06/787,844 patent/US4681882A/en not_active Expired - Fee Related
- 1985-10-17 CA CA000493181A patent/CA1257261A/en not_active Expired
- 1985-10-17 JP JP60230048A patent/JPS61100582A/ja active Pending
- 1985-10-17 ZA ZA857989A patent/ZA857989B/xx unknown
- 1985-10-18 EP EP85113270A patent/EP0180834B1/de not_active Expired
- 1985-10-18 DK DK478585A patent/DK478585A/da not_active Application Discontinuation
- 1985-10-18 AT AT85113270T patent/ATE45949T1/de not_active IP Right Cessation
- 1985-10-18 ES ES548008A patent/ES8605519A1/es not_active Expired
- 1985-10-18 DE DE8585113270T patent/DE3572663D1/de not_active Expired
- 1985-10-18 GR GR852529A patent/GR852529B/el unknown
- 1985-10-18 HU HU854037A patent/HU194227B/hu unknown
- 1985-10-18 DD DD85281879A patent/DD239794A5/de not_active IP Right Cessation
- 1985-10-18 AU AU48856/85A patent/AU579413B2/en not_active Ceased
-
1987
- 1987-05-29 US US07/055,816 patent/US4762837A/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4361700A (en) * | 1980-05-20 | 1982-11-30 | James S. Waldron | Pyridopyrimidinone derivatives |
US4560753A (en) * | 1982-11-05 | 1985-12-24 | Sterling Drug Inc. | 2-Substituted-pyrido[2,3-d]pyrimidin-5(8H)-ones |
Non-Patent Citations (2)
Title |
---|
Gorlitzer et al., Arch. Pharm. (Weinheim) vol. 314, pp. 938 949 (1981). * |
Gorlitzer et al., Arch. Pharm. (Weinheim) vol. 314, pp. 938-949 (1981). |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5059602A (en) * | 1990-08-27 | 1991-10-22 | Hoechst-Roussel Pharmaceuticals Inc. | 4-substituted dihydropyrido(4,3-d)pyrimidines as analgesics and topical antiinflammatory agents for the treatment of skin disorders |
WO2003009815A2 (en) | 2001-07-25 | 2003-02-06 | Biomarin Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
EP2147679A2 (de) | 2001-07-25 | 2010-01-27 | Raptor Pharmaceutical Inc. | Zusammensetzungen und Verfahren zur Modulierung von Blut-Hirn-Schrankentransporten |
WO2006116718A2 (en) | 2005-04-28 | 2006-11-02 | Proteus Biomedical, Inc. | Pharma-informatics system |
EP2392258A1 (de) | 2005-04-28 | 2011-12-07 | Proteus Biomedical, Inc. | Pharma-Informatiksystem |
EP3827747A1 (de) | 2005-04-28 | 2021-06-02 | Otsuka Pharmaceutical Co., Ltd. | Pharmainformatiksystem |
US8404709B2 (en) | 2006-06-07 | 2013-03-26 | Bayer Intellectual Property Gmbh | Substituted 4-aryl-1,4-dihydro-1,6-naphthyridines and use thereof |
US20100035902A1 (en) * | 2006-06-07 | 2010-02-11 | Bayer Healthcare Ag | 5-aryl-substituted dihydropyridopyrimidines and dihydropyridazines and use thereof as mineral corticoid antagonists |
US20100305052A1 (en) * | 2006-06-07 | 2010-12-02 | Bayer Schering Pharma Aktiengesellschaft | Substituted 4-aryl-1,4-dihydro-1,6-naphthyridines and use thereof |
US8399471B2 (en) | 2006-06-07 | 2013-03-19 | Bayer Intellectual Property Gmbh | Aryl-or heteroaryl-substituted pyrido[2,3-d] pyrimidines and pharmaceutical compositions of the same |
WO2008036682A2 (en) | 2006-09-18 | 2008-03-27 | Raptor Pharmaceutical Inc. | Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates |
WO2010095940A2 (en) | 2009-02-20 | 2010-08-26 | To-Bbb Holding B.V. | Glutathione-based drug delivery system |
EP4218718A2 (de) | 2009-05-06 | 2023-08-02 | Laboratory Skin Care, Inc. | Dermale freisetzungszusammensetzung mit wirkstoff-calciumphosphat-partikelkomplexen und anwendungsverfahren |
WO2012044761A1 (en) | 2010-09-29 | 2012-04-05 | University Of North Carolina At Wilmington | Ladder-frame polyether conjugates |
Also Published As
Publication number | Publication date |
---|---|
CN85107614A (zh) | 1986-07-16 |
CN1004274B (zh) | 1989-05-24 |
EP0180834B1 (de) | 1989-08-30 |
GR852529B (de) | 1986-02-19 |
CA1257261A (en) | 1989-07-11 |
ATE45949T1 (de) | 1989-09-15 |
HUT39181A (en) | 1986-08-28 |
DK478585D0 (da) | 1985-10-18 |
EP0180834A1 (de) | 1986-05-14 |
DD239794A5 (de) | 1986-10-08 |
DE3438351A1 (de) | 1986-04-24 |
AU4885685A (en) | 1986-04-24 |
ES548008A0 (es) | 1986-03-16 |
JPS61100582A (ja) | 1986-05-19 |
ES8605519A1 (es) | 1986-03-16 |
AU579413B2 (en) | 1988-11-24 |
DE3572663D1 (en) | 1989-10-05 |
ZA857989B (en) | 1986-06-25 |
DK478585A (da) | 1986-04-20 |
HU194227B (en) | 1988-01-28 |
US4762837A (en) | 1988-08-09 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: GODECKE AKTIENGESELLSCHAFT, BERLIN, SALZUFER 16, A Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:KLEINSCHROTH, JURGEN;SATZINGER, GERHARD;MANNHARDT, KARL;AND OTHERS;REEL/FRAME:004469/0272 Effective date: 19851001 |
|
FPAY | Fee payment |
Year of fee payment: 4 |
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REMI | Maintenance fee reminder mailed | ||
LAPS | Lapse for failure to pay maintenance fees | ||
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 19950726 |
|
STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |